HCID 86591159, compound → HCID 69020431, compound

HRID 860797Notes

Reaction equation

HRID 860797 reaction equation
[N:1]([CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)OCC[O:15]2)=[CH:10][C:9]=1[C:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:6])=[N+]=[N-]>C1COCC1.[Pd].C(O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:14]([C:11]2[CH:12]=[CH:13][C:8]3[NH:7][C:5](=[O:6])[CH2:4][N:1]=[C:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:9]=3[CH:10]=2)=[O:15])=[CH:20][CH:21]=1

Participants

5

Reactant 1

HCID 86591159HCID 86591159, compound

Product 1

HCID 69020431HCID 69020431, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate (26) (0.1052 mol) in THF (220 ml) was hydrogenated with Pd/C (0.6 g) as a catalyst at room temperature for 8 h under a 2 bar pressure in a Parr apparatus. After uptake of H2, the catalyst was filtered over celite and the filtrate was evaporated till dryness. The residue (47.9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1) (35–70 μm). The pure fractions were collected and evaporated and the residue was crystallized from 2-propanone/DIPE giving 14.86 g (31%). A sample (1.35 g) was taken up in hot ethanol and filtered off, yielding 0.93 g (70%) of 7-(4-chlorobenzoyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (intermediate 27), mp. 230° C.

Workup

  1. filtrationAfter uptake of H2, the catalyst was filtered over celite
  2. customthe filtrate was evaporated till dryness
  3. customThe residue (47.9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1) (35–70 μm)
  4. customThe pure fractions were collected
  5. customevaporated
  6. customthe residue was crystallized from 2-propanone/DIPE
  7. customgiving 14.86 g (31%)
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-323e36800c2a429395652dba459cef85
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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